Allyl chloride → HCID 131734422, compound

HRID 587908Notes

Reaction equation

OC1C(C)=C(O)C=CC=1C=O.C(Cl)C=C.C(N(CC)C(C)C)(C)C.C([O:28][C:29]1[C:36]([CH3:37])=[C:35]([O:38][CH2:39][CH:40]=[CH2:41])[CH:34]=[CH:33][C:30]=1[CH:31]=[O:32])C=C>>[CH2:39]([O:38][C:35]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[C:29]([OH:28])[C:36]=1[CH3:37])[CH:40]=[CH2:41]

Participants

Reactant 4

HCID 7850Allyl chloride

HCID 803952,4-Dihydroxy-3-methylbenzaldehyde

HCID 81531Diisopropylethylamine

HCID 131734423HCID 131734423, compound

Product 1

HCID 131734422HCID 131734422, compound

Procedure

By following Example 2 procedure, 5.0 g of 2,4-dihydroxy-3-methylbenzaldehyde was reacted with 8.35 g of allyl chloride and 5.1 g of N,N-diisopropylethylamine to get 8.41 g of crude title product containing 12% of 2,4-bis(allyloxy)-3-methylbenzaldehyde by GC. Crude product was purified by column chromatography to get the title compound as liquid. IR (neat): 3280, 3088, 3024, 2988, 2926, 2838, 2748, 1645, 1585, 1499, 1452, 1427, 1388, 1353, 1330, 1290, 1250, 1182, 1110, 1022, 990, 928, 891, 788, 758, 715, and 646 cm−1. 1H-NMR (CDCl3, 400 MHz): δ 11.45 (s, 1H, exch. with D2O, OH), 9.70 (s, 1H, CHO), 7.34 (d, J=8.8 Hz, 1H, H-6), 6.53 (d, J=8.8 Hz, 1H, H-5), 6.06 (m, 1H, CH═CH2), 5.44 (dq, J=1.6, 19.2 Hz, 1H, CH═CH2), 5.32 (dq, J=1.2, 10.8 Hz, 1H, CH═CH2), 4.64 (dt, J=1.6, 4.8 Hz, 2H, CH2═CHCH2), 2.13 (s, 3H, ArCH3). 13C NMR (CDCl3, 100 MHz): δ 194.60 (CHO), 163.17 (C-4), 160.99 (C-2), 133.00 (CH2═CH); 132.38 (C-5), 117.55 (CH2═CH), 113.48 (C-1), 103.75 (C-5), 68.90 (OCH2), 7.30 (ArCH3). Mass (EI-MS): 192.1 (M), 191.3 (M−1).

Workup

customto get 8.41 g of crude title product
customCrude product was purified by column chromatography

Sources & evidence

ORD record: ord-b4fe82e1ac7d4949a3c0938772138fbe
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227948B2

Reaction notes

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