Acetic Acid → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzoic Acid

HRID 631781Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:17])[F:16])[CH:9]=[O:10])[CH2:3][CH2:2]1.C(O)(=[O:20])C.S(=O)(=O)(O)N.[Cl-].[Na+]>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=2[O:14][CH:15]([F:16])[F:17])[C:9]([OH:20])=[O:10])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 7.5 °C

Procedure

40 g of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzaldehyde 160 mL of glacial acetic acid and 32.0 g of sulphamic acid (2.0 eq) were loaded in a reactor. The mixture was cooled at 5-10° C. and the temperature was not allowed to exceed 20° C., adding slowly a previously prepared solution of 44.77 g of sodium chloride and 61 mL of deionised water. After the addition, the reaction was kept for 1 hour at 15-20° C. 450 mL of deionised water was loaded and then it was cooled at 0-5° C. and kept for 1 h at this temperature. The solid was filtered and washed four times with 200 mL of deionised water. The product was dried for 15 h at 40° C., obtaining 36 g (yield 85%) of 3-(cyclopropylmethoxy)-4-(difluoromethoxy)-benzoic acid (II) as solid.

Workup

customto exceed 20° C.
additionAfter the addition
temperatureit was cooled at 0-5° C.
waitkept for 1 h at this temperature
filtrationThe solid was filtered
washwashed four times with 200 mL of deionised water
customThe product was dried for 15 h at 40° C.

Sources & evidence

ORD record: ord-137d8b51a49d4c059e07ba72f7b8b027
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321726B2

Reaction notes

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