3-Methoxybenzyl alcohol → 5-HYDROXYPHTHALIDE

HRID 1277856Notes

Reaction equation

HRID 1277856 reaction equation
COC1C=C(C=CC=1)CO.C[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:18](=[O:19])[O:17][CH2:16]2.COC1C=CC=C2C=1C(=O)OC2>>[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:18](=[O:19])[O:17][CH2:16]2

Participants

4

Reactant 3

HCID 814373-Methoxybenzyl alcoholHCID 105350125-methoxy-3H-isobenzofuran-1-oneHCID 109865837-methoxy-3H-isobenzofuran-1-one

Product 1

HCID 2318865-HYDROXYPHTHALIDE

Procedure

The reactions are also highly stereo- and regiospecific. Thus, thallation-carbonylation of cis- and trans-2-phenylcyclohexanoles (examples 7 and 8) provide exclusively the cis and trans fused tricyclic lactones respectively. Substituents on the aromatic ring are also observed to effect a very pronounced directive effect. For example, thallation-carbonylation of m-methoxybenzyl alcohol affords the 5-methoxyphthalide in 89% yield and only a trace of the 7-methoxyphthalide (example 4). Similarly, m-hydroxybenzyl alcohol affords a 95% isolated yield of pure 5-hydroxyphthalide (example 5).

Workup

  1. customSimilarly, m-hydroxybenzyl alcohol affords a 95%

Sources & evidence

ORD record
ord-79eb56718e6a44f9b2d722b2fe748742
Source dataset
uspto-grants-1981_07
Patent number
US04279823

Reaction notes

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