Ethanol → Ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-3-yl)ethynyl]benzoate

Reaction equation

[BH4-:1].[CH2:29]1[O:30][CH2:31][CH2:32][CH2:33]1.[CH3:34][CH2:35][OH:36].[CH3:3][C:4]1([CH3:28])[CH2:5][CH2:6][C:7](=[O:27])[c:8]2[cH:9][c:10]([C:14]#[C:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22][CH2:23][CH3:24])[cH:25][cH:26]3)[cH:11][cH:12][c:13]21.[Na+:2].[OH2:37]>>[CH3:3][C:4]1([CH3:28])[CH2:5][CH2:6][CH:7]([OH:27])[c:8]2[cH:9][c:10]([C:14]#[C:15][c:16]3[cH:17][cH:18][c:19]([C:20](=[O:21])[O:22][CH2:23][CH3:24])[cH:25][cH:26]3)[cH:11][cH:12][c:13]21